diff --git a/event/cmdschema/content.go b/event/cmdschema/content.go
index e7f362ed..ce07c4c0 100644
--- a/event/cmdschema/content.go
+++ b/event/cmdschema/content.go
@@ -69,7 +69,8 @@ func (ec *EventContent) Equals(other *EventContent) bool {
 	return ec.Command == other.Command &&
 		slices.Equal(ec.Aliases, other.Aliases) &&
 		slices.EqualFunc(ec.Parameters, other.Parameters, (*Parameter).Equals) &&
-		ec.Description.Equals(other.Description)
+		ec.Description.Equals(other.Description) &&
+		ec.TailParam == other.TailParam
 }
 
 func init() {
diff --git a/event/cmdschema/parse.go b/event/cmdschema/parse.go
index 91a02827..fbb8b671 100644
--- a/event/cmdschema/parse.go
+++ b/event/cmdschema/parse.go
@@ -92,7 +92,7 @@ func (ec *EventContent) ParseArguments(input string) (json.RawMessage, error) {
 			retErr = err
 		}
 	}
-	processParameter := func(param *Parameter, isLast, isNamed bool) {
+	processParameter := func(param *Parameter, isLast, isTail, isNamed bool) {
 		origInput := input
 		var nextVal string
 		var wasQuoted bool
@@ -135,8 +135,8 @@ func (ec *EventContent) ParseArguments(input string) (json.RawMessage, error) {
 			args[param.Key] = collector
 		} else {
 			nextVal, input, wasQuoted = parseQuoted(input)
-			if isLast && !wasQuoted && len(input) > 0 && !strings.Contains(input, "--") {
-				// If the last argument is not quoted and doesn't have flags, just treat the rest of the string
+			if (isLast || isTail) && !wasQuoted && len(input) > 0 {
+				// If the last argument is not quoted, just treat the rest of the string
 				// as the argument without escapes (arguments with escapes should be quoted).
 				nextVal += " " + input
 				input = ""
@@ -175,7 +175,7 @@ func (ec *EventContent) ParseArguments(input string) (json.RawMessage, error) {
 				// Trim the equals sign, but leave spaces alone to let parseQuoted treat it as empty input
 				input = strings.TrimPrefix(input[nameEndIdx:], "=")
 				skipParams[paramIdx] = true
-				processParameter(overrideParam, false, true)
+				processParameter(overrideParam, false, false, true)
 			} else {
 				break
 			}
@@ -184,7 +184,7 @@ func (ec *EventContent) ParseArguments(input string) (json.RawMessage, error) {
 		if skipParams[i] || (param.Optional && !isTail) {
 			continue
 		}
-		processParameter(param, i == len(ec.Parameters)-1 || isTail, false)
+		processParameter(param, i == len(ec.Parameters)-1, isTail, false)
 	}
 	jsonArgs, marshalErr := json.Marshal(args)
 	if marshalErr != nil {
diff --git a/event/cmdschema/testdata/commands/flags.json b/event/cmdschema/testdata/commands/flags.json
index 469986f0..89f0f334 100644
--- a/event/cmdschema/testdata/commands/flags.json
+++ b/event/cmdschema/testdata/commands/flags.json
@@ -93,24 +93,6 @@
 				"woof": false
 			}
 		},
-		{
-			"name": "named flag at end",
-			"input": "/flag mrrp @user:example.com --woof=yes",
-			"output": {
-				"meow": "mrrp",
-				"user": "@user:example.com",
-				"woof": true
-			}
-		},
-		{
-			"name": "named flag at end without value",
-			"input": "/flag mrrp @user:example.com --woof",
-			"output": {
-				"meow": "mrrp",
-				"user": "@user:example.com",
-				"woof": true
-			}
-		},
 		{
 			"name": "all variables named",
 			"input": "/flag --woof=no --meow=mrrp --user=@user:example.com",
diff --git a/event/cmdschema/testdata/commands/tail.json b/event/cmdschema/testdata/commands/tail.json
new file mode 100644
index 00000000..db6f79d4
--- /dev/null
+++ b/event/cmdschema/testdata/commands/tail.json
@@ -0,0 +1,59 @@
+{
+	"spec": {
+		"command": "tail",
+		"source": "@testbot",
+		"parameters": [
+			{
+				"key": "meow",
+				"schema": {
+					"schema_type": "primitive",
+					"type": "string"
+				}
+			},
+			{
+				"key": "reason",
+				"schema": {
+					"schema_type": "primitive",
+					"type": "string"
+				},
+				"optional": true
+			},
+			{
+				"key": "woof",
+				"schema": {
+					"schema_type": "primitive",
+					"type": "boolean"
+				},
+				"optional": true
+			}
+		],
+		"fi.mau.tail_parameter": "reason"
+	},
+	"tests": [
+		{
+			"name": "no tail or flag",
+			"input": "/tail mrrp",
+			"output": {
+				"meow": "mrrp",
+				"reason": ""
+			}
+		},
+		{
+			"name": "tail, no flag",
+			"input": "/tail mrrp meow meow",
+			"output": {
+				"meow": "mrrp",
+				"reason": "meow meow"
+			}
+		},
+		{
+			"name": "flag before tail",
+			"input": "/tail mrrp --woof meow meow",
+			"output": {
+				"meow": "mrrp",
+				"reason": "meow meow",
+				"woof": true
+			}
+		}
+	]
+}